# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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data_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 N'
_chemical_formula_sum            'C23 H19 N'
_chemical_formula_weight         309.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.6312(15)
_cell_length_b                   9.0492(10)
_cell_length_c                   27.107(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3343.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      28.38

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9777
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25483
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6411
_reflns_number_gt                5656
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0566P)²+0.3811P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0064(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_number_reflns         6411
_refine_ls_number_parameters     436
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0990
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.72032(11) 0.28563(18) 0.17891(7) 0.0428(4) Uani 1 1 d . . .
N2 N 0.96723(12) 0.28229(18) 0.49009(7) 0.0426(4) Uani 1 1 d . . .
C1 C 0.63443(12) 0.30421(19) 0.15347(7) 0.0411(4) Uani 1 1 d . . .
C2 C 0.62408(14) 0.43502(19) 0.12548(7) 0.0491(4) Uani 1 1 d . . .
H2 H 0.6742 0.5047 0.1254 0.059 Uiso 1 1 calc R . .
C3 C 0.54140(16) 0.4598(2) 0.09862(8) 0.0550(5) Uani 1 1 d . . .
H3 H 0.5354 0.5459 0.0801 0.066 Uiso 1 1 calc R . .
C4 C 0.46563(16) 0.3561(2) 0.09883(8) 0.0571(5) Uani 1 1 d . . .
H4 H 0.4100 0.3724 0.0797 0.069 Uiso 1 1 calc R . .
C5 C 0.47222(18) 0.2302(2) 0.12691(11) 0.0536(6) Uani 1 1 d . . .
H5 H 0.4200 0.1641 0.1277 0.064 Uiso 1 1 calc R . .
C6 C 0.55752(13) 0.2004(2) 0.15460(7) 0.0423(4) Uani 1 1 d . . .
C7 C 0.56983(12) 0.07027(19) 0.18373(7) 0.0422(4) Uani 1 1 d . . .
C8 C 0.65915(12) 0.04871(17) 0.20686(6) 0.0405(4) Uani 1 1 d . . .
C9 C 0.73234(12) 0.16086(19) 0.20378(7) 0.0394(4) Uani 1 1 d . . .
C10 C 0.82818(12) 0.14701(17) 0.23013(7) 0.0412(4) Uani 1 1 d . . .
C11 C 0.85741(19) 0.25483(19) 0.26358(10) 0.0486(6) Uani 1 1 d . . .
H11 H 0.8158 0.3335 0.2707 0.058 Uiso 1 1 calc R . .
C12 C 0.9477(2) 0.2456(2) 0.28625(13) 0.0633(8) Uani 1 1 d . . .
H12 H 0.9668 0.3190 0.3083 0.076 Uiso 1 1 calc R . .
C13 C 1.00939(15) 0.1301(3) 0.27679(9) 0.0657(6) Uani 1 1 d . . .
H13 H 1.0697 0.1239 0.2927 0.079 Uiso 1 1 calc R . .
C14 C 0.98193(15) 0.0235(2) 0.24366(9) 0.0602(5) Uani 1 1 d . . .
H14 H 1.0242 -0.0544 0.2367 0.072 Uiso 1 1 calc R . .
C15 C 0.89197(13) 0.0312(2) 0.22053(8) 0.0509(4) Uani 1 1 d . . .
H15 H 0.8739 -0.0421 0.1983 0.061 Uiso 1 1 calc R . .
C16 C 0.67866(12) -0.0875(2) 0.23645(7) 0.0428(4) Uani 1 1 d . . .
C17 C 0.67648(15) -0.0851(2) 0.28717(8) 0.0561(5) Uani 1 1 d . . .
H17 H 0.6616 0.0023 0.3036 0.067 Uiso 1 1 calc R . .
C18 C 0.69640(19) -0.2123(4) 0.31397(10) 0.0697(7) Uani 1 1 d . . .
H18 H 0.6931 -0.2101 0.3482 0.084 Uiso 1 1 calc R . .
C19 C 0.72097(16) -0.3415(3) 0.29036(11) 0.0666(6) Uani 1 1 d . . .
H19 H 0.7358 -0.4258 0.3085 0.080 Uiso 1 1 calc R . .
C20 C 0.72342(15) -0.3450(2) 0.24021(9) 0.0585(5) Uani 1 1 d . . .
H20 H 0.7394 -0.4324 0.2240 0.070 Uiso 1 1 calc R . .
C21 C 0.70227(15) -0.2195(2) 0.21314(10) 0.0517(5) Uani 1 1 d . . .
H21 H 0.7039 -0.2236 0.1789 0.062 Uiso 1 1 calc R . .
C22 C 0.48488(14) -0.0368(2) 0.19068(8) 0.0540(5) Uani 1 1 d . . .
H22A H 0.4247 0.0196 0.1939 0.065 Uiso 1 1 calc R . .
H22B H 0.4947 -0.0905 0.2212 0.065 Uiso 1 1 calc R . .
C23 C 0.47245(18) -0.1476(2) 0.14887(10) 0.0718(6) Uani 1 1 d . . .
H23A H 0.4672 -0.0958 0.1181 0.108 Uiso 1 1 calc R . .
H23B H 0.4141 -0.2047 0.1543 0.108 Uiso 1 1 calc R . .
H23C H 0.5283 -0.2122 0.1479 0.108 Uiso 1 1 calc R . .
C24 C 0.88135(12) 0.3023(2) 0.51560(6) 0.0407(4) Uani 1 1 d . . .
C25 C 0.87112(14) 0.4325(2) 0.54381(7) 0.0492(4) Uani 1 1 d . . .
H25 H 0.9212 0.5023 0.5439 0.059 Uiso 1 1 calc R . .
C26 C 0.78830(15) 0.4572(2) 0.57101(8) 0.0550(5) Uani 1 1 d . . .
H26 H 0.7829 0.5422 0.5901 0.066 Uiso 1 1 calc R . .
C27 C 0.71191(15) 0.3546(2) 0.57003(8) 0.0564(5) Uani 1 1 d . . .
H27 H 0.6555 0.3723 0.5884 0.068 Uiso 1 1 calc R . .
C28 C 0.71855(17) 0.2292(2) 0.54261(11) 0.0512(6) Uani 1 1 d . . .
H28 H 0.6664 0.1629 0.5423 0.061 Uiso 1 1 calc R . .
C29 C 0.80379(12) 0.1981(2) 0.51452(7) 0.0411(4) Uani 1 1 d . . .
C30 C 0.81606(12) 0.06722(18) 0.48537(6) 0.0409(4) Uani 1 1 d . . .
C31 C 0.90511(12) 0.04534(17) 0.46248(6) 0.0391(3) Uani 1 1 d . . .
C32 C 0.97888(12) 0.15785(18) 0.46559(7) 0.0393(4) Uani 1 1 d . . .
C33 C 1.07521(12) 0.14218(17) 0.43991(6) 0.0398(4) Uani 1 1 d . . .
C34 C 1.10806(19) 0.25337(19) 0.40957(11) 0.0508(6) Uani 1 1 d . . .
H34 H 1.0690 0.3360 0.4041 0.061 Uiso 1 1 calc R . .
C35 C 1.1997(2) 0.2429(3) 0.38686(12) 0.0596(8) Uani 1 1 d . . .
H35 H 1.2206 0.3174 0.3657 0.072 Uiso 1 1 calc R . .
C36 C 1.25907(15) 0.1234(2) 0.39561(8) 0.0585(5) Uani 1 1 d . . .
H36 H 1.3206 0.1175 0.3809 0.070 Uiso 1 1 calc R . .
C37 C 1.22703(14) 0.0124(2) 0.42621(9) 0.0586(5) Uani 1 1 d . . .
H37 H 1.2670 -0.0690 0.4321 0.070 Uiso 1 1 calc R . .
C38 C 1.13588(13) 0.0210(2) 0.44820(8) 0.0504(4) Uani 1 1 d . . .
H38 H 1.1148 -0.0549 0.4688 0.060 Uiso 1 1 calc R . .
C39 C 0.92526(12) -0.09183(18) 0.43316(7) 0.0412(4) Uani 1 1 d . . .
C40 C 0.92610(15) -0.0892(2) 0.38239(7) 0.0523(5) Uani 1 1 d . . .
H40 H 0.9119 -0.0017 0.3659 0.063 Uiso 1 1 calc R . .
C41 C 0.9479(2) -0.2152(3) 0.35558(10) 0.0639(6) Uani 1 1 d . . .
H41 H 0.9484 -0.2122 0.3213 0.077 Uiso 1 1 calc R . .
C42 C 0.96878(16) -0.3452(3) 0.37989(10) 0.0619(6) Uani 1 1 d . . .
H42 H 0.9835 -0.4298 0.3619 0.074 Uiso 1 1 calc R . .
C43 C 0.96806(15) -0.3509(2) 0.43063(9) 0.0552(5) Uani 1 1 d . . .
H43 H 0.9826 -0.4387 0.4469 0.066 Uiso 1 1 calc R . .
C44 C 0.94558(15) -0.2247(2) 0.45716(9) 0.0466(5) Uani 1 1 d . . .
H44 H 0.9440 -0.2286 0.4914 0.056 Uiso 1 1 calc R . .
C45 C 0.73197(13) -0.0394(2) 0.47923(8) 0.0502(4) Uani 1 1 d . . .
H45A H 0.7419 -0.0946 0.4490 0.060 Uiso 1 1 calc R . .
H45B H 0.6719 0.0169 0.4755 0.060 Uiso 1 1 calc R . .
C46 C 0.71869(18) -0.1482(2) 0.52122(10) 0.0697(6) Uani 1 1 d . . .
H46A H 0.7772 -0.2061 0.5249 0.105 Uiso 1 1 calc R . .
H46B H 0.6643 -0.2122 0.5141 0.105 Uiso 1 1 calc R . .
H46C H 0.7061 -0.0952 0.5512 0.105 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.325(2) . ?
N1 C1 1.369(2) . ?
N2 C32 1.317(2) . ?
N2 C24 1.372(2) . ?
C1 C6 1.408(3) . ?
C1 C2 1.413(3) . ?
C2 C3 1.360(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.428(3) . ?
C7 C8 1.383(2) . ?
C7 C22 1.521(2) . ?
C8 C9 1.426(2) . ?
C8 C16 1.495(2) . ?
C9 C10 1.494(2) . ?
C10 C15 1.386(2) . ?
C10 C11 1.390(3) . ?
C11 C12 1.378(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.375(3) . ?
C16 C21 1.389(3) . ?
C17 C18 1.388(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.360(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.382(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.523(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.412(3) . ?
C24 C29 1.417(2) . ?
C25 C26 1.367(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.395(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.360(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.417(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.433(2) . ?
C30 C31 1.378(2) . ?
C30 C45 1.508(2) . ?
C31 C32 1.433(2) . ?
C31 C39 1.499(2) . ?
C32 C33 1.493(2) . ?
C33 C34 1.374(3) . ?
C33 C38 1.392(2) . ?
C34 C35 1.396(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.371(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.374(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.380(3) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 C40 1.377(3) . ?
C39 C44 1.395(3) . ?
C40 C41 1.385(3) . ?
C40 H40 0.9300 . ?
C41 C42 1.378(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.377(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.383(3) . ?
C43 H43 0.9300 . ?
C44 H44 0.9300 . ?
C45 C46 1.516(3) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C1 117.81(16) . . ?
C32 N2 C24 118.03(16) . . ?
N1 C1 C6 122.94(16) . . ?
N1 C1 C2 117.30(16) . . ?
C6 C1 C2 119.76(16) . . ?
C3 C2 C1 120.55(17) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.99(18) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.34(18) . . ?
C1 C6 C7 118.35(16) . . ?
C5 C6 C7 123.31(18) . . ?
C8 C7 C6 118.06(15) . . ?
C8 C7 C22 121.60(16) . . ?
C6 C7 C22 120.28(16) . . ?
C7 C8 C9 119.27(15) . . ?
C7 C8 C16 121.07(14) . . ?
C9 C8 C16 119.62(15) . . ?
N1 C9 C8 123.36(16) . . ?
N1 C9 C10 115.00(14) . . ?
C8 C9 C10 121.61(15) . . ?
C15 C10 C11 118.24(18) . . ?
C15 C10 C9 121.47(16) . . ?
C11 C10 C9 120.23(16) . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 119.6(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.36(19) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.70(19) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C17 C16 C21 118.2(2) . . ?
C17 C16 C8 121.29(18) . . ?
C21 C16 C8 120.44(18) . . ?
C16 C17 C18 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 120.6(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 119.4(2) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 120.4(2) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.9(2) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
C7 C22 C23 114.32(17) . . ?
C7 C22 H22A 108.7 . . ?
C23 C22 H22A 108.7 . . ?
C7 C22 H22B 108.7 . . ?
C23 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 C25 117.86(16) . . ?
N2 C24 C29 122.59(16) . . ?
C25 C24 C29 119.55(16) . . ?
C26 C25 C24 120.67(18) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C27 119.82(18) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C28 C27 C26 121.09(19) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C29 120.9(2) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C24 C29 C28 117.93(18) . . ?
C24 C29 C30 118.30(15) . . ?
C28 C29 C30 123.77(17) . . ?
C31 C30 C29 118.02(15) . . ?
C31 C30 C45 121.88(15) . . ?
C29 C30 C45 120.07(15) . . ?
C30 C31 C32 119.31(15) . . ?
C30 C31 C39 121.27(14) . . ?
C32 C31 C39 119.39(14) . . ?
N2 C32 C31 123.53(16) . . ?
N2 C32 C33 114.99(14) . . ?
C31 C32 C33 121.47(15) . . ?
C34 C33 C38 118.68(18) . . ?
C34 C33 C32 119.74(16) . . ?
C38 C33 C32 121.47(15) . . ?
C33 C34 C35 120.38(19) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C36 C35 C34 120.3(2) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C36 C37 119.6(2) . . ?
C35 C36 H36 120.2 . . ?
C37 C36 H36 120.2 . . ?
C36 C37 C38 120.40(19) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
C37 C38 C33 120.62(18) . . ?
C37 C38 H38 119.7 . . ?
C33 C38 H38 119.7 . . ?
C40 C39 C44 118.64(19) . . ?
C40 C39 C31 121.14(17) . . ?
C44 C39 C31 120.20(17) . . ?
C39 C40 C41 120.8(2) . . ?
C39 C40 H40 119.6 . . ?
C41 C40 H40 119.6 . . ?
C42 C41 C40 119.8(2) . . ?
C42 C41 H41 120.1 . . ?
C40 C41 H41 120.1 . . ?
C43 C42 C41 120.5(2) . . ?
C43 C42 H42 119.7 . . ?
C41 C42 H42 119.7 . . ?
C42 C43 C44 119.4(2) . . ?
C42 C43 H43 120.3 . . ?
C44 C43 H43 120.3 . . ?
C43 C44 C39 120.9(2) . . ?
C43 C44 H44 119.6 . . ?
C39 C44 H44 119.6 . . ?
C30 C45 C46 115.06(16) . . ?
C30 C45 H45A 108.5 . . ?
C46 C45 H45A 108.5 . . ?
C30 C45 H45B 108.5 . . ?
C46 C45 H45B 108.5 . . ?
H45A C45 H45B 107.5 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C6 3.1(3) . . . . ?
C9 N1 C1 C2 -177.50(17) . . . . ?
N1 C1 C2 C3 178.92(18) . . . . ?
C6 C1 C2 C3 -1.6(3) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C3 C4 C5 C6 -2.6(4) . . . . ?
N1 C1 C6 C5 -179.8(2) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
N1 C1 C6 C7 0.2(3) . . . . ?
C2 C1 C6 C7 -179.22(16) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
C4 C5 C6 C7 -178.70(19) . . . . ?
C1 C6 C7 C8 -4.0(2) . . . . ?
C5 C6 C7 C8 176.1(2) . . . . ?
C1 C6 C7 C22 173.26(16) . . . . ?
C5 C6 C7 C22 -6.7(3) . . . . ?
C6 C7 C8 C9 4.5(2) . . . . ?
C22 C7 C8 C9 -172.71(16) . . . . ?
C6 C7 C8 C16 -177.75(15) . . . . ?
C22 C7 C8 C16 5.1(3) . . . . ?
C1 N1 C9 C8 -2.6(3) . . . . ?
C1 N1 C9 C10 179.22(15) . . . . ?
C7 C8 C9 N1 -1.2(3) . . . . ?
C16 C8 C9 N1 -179.05(17) . . . . ?
C7 C8 C9 C10 176.85(16) . . . . ?
C16 C8 C9 C10 -1.0(2) . . . . ?
N1 C9 C10 C15 -121.64(18) . . . . ?
C8 C9 C10 C15 60.1(2) . . . . ?
N1 C9 C10 C11 55.5(2) . . . . ?
C8 C9 C10 C11 -122.7(2) . . . . ?
C15 C10 C11 C12 0.1(3) . . . . ?
C9 C10 C11 C12 -177.1(2) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C11 C12 C13 C14 1.2(4) . . . . ?
C12 C13 C14 C15 -1.0(4) . . . . ?
C13 C14 C15 C10 0.4(3) . . . . ?
C11 C10 C15 C14 0.1(3) . . . . ?
C9 C10 C15 C14 177.24(17) . . . . ?
C7 C8 C16 C17 -102.9(2) . . . . ?
C9 C8 C16 C17 74.8(2) . . . . ?
C7 C8 C16 C21 78.9(2) . . . . ?
C9 C8 C16 C21 -103.3(2) . . . . ?
C21 C16 C17 C18 -0.7(3) . . . . ?
C8 C16 C17 C18 -178.93(18) . . . . ?
C16 C17 C18 C19 1.6(4) . . . . ?
C17 C18 C19 C20 -1.6(4) . . . . ?
C18 C19 C20 C21 0.6(4) . . . . ?
C19 C20 C21 C16 0.3(3) . . . . ?
C17 C16 C21 C20 -0.3(3) . . . . ?
C8 C16 C21 C20 177.98(18) . . . . ?
C8 C7 C22 C23 -99.4(2) . . . . ?
C6 C7 C22 C23 83.5(2) . . . . ?
C32 N2 C24 C25 176.91(17) . . . . ?
C32 N2 C24 C29 -3.2(3) . . . . ?
N2 C24 C25 C26 -178.41(18) . . . . ?
C29 C24 C25 C26 1.7(3) . . . . ?
C24 C25 C26 C27 -1.6(3) . . . . ?
C25 C26 C27 C28 0.4(3) . . . . ?
C26 C27 C28 C29 0.6(4) . . . . ?
N2 C24 C29 C28 179.48(19) . . . . ?
C25 C24 C29 C28 -0.6(3) . . . . ?
N2 C24 C29 C30 -0.2(3) . . . . ?
C25 C24 C29 C30 179.68(15) . . . . ?
C27 C28 C29 C24 -0.5(3) . . . . ?
C27 C28 C29 C30 179.17(19) . . . . ?
C24 C29 C30 C31 4.1(2) . . . . ?
C28 C29 C30 C31 -175.63(19) . . . . ?
C24 C29 C30 C45 -174.14(16) . . . . ?
C28 C29 C30 C45 6.2(3) . . . . ?
C29 C30 C31 C32 -4.5(2) . . . . ?
C45 C30 C31 C32 173.66(16) . . . . ?
C29 C30 C31 C39 177.32(15) . . . . ?
C45 C30 C31 C39 -4.5(3) . . . . ?
C24 N2 C32 C31 2.8(3) . . . . ?
C24 N2 C32 C33 -178.35(15) . . . . ?
C30 C31 C32 N2 1.1(3) . . . . ?
C39 C31 C32 N2 179.34(17) . . . . ?
C30 C31 C32 C33 -177.69(15) . . . . ?
C39 C31 C32 C33 0.5(2) . . . . ?
N2 C32 C33 C34 -51.1(3) . . . . ?
C31 C32 C33 C34 127.8(2) . . . . ?
N2 C32 C33 C38 125.01(18) . . . . ?
C31 C32 C33 C38 -56.1(2) . . . . ?
C38 C33 C34 C35 1.3(3) . . . . ?
C32 C33 C34 C35 177.4(2) . . . . ?
C33 C34 C35 C36 -1.7(4) . . . . ?
C34 C35 C36 C37 1.2(4) . . . . ?
C35 C36 C37 C38 -0.2(3) . . . . ?
C36 C37 C38 C33 -0.2(3) . . . . ?
C34 C33 C38 C37 -0.3(3) . . . . ?
C32 C33 C38 C37 -176.40(17) . . . . ?
C30 C31 C39 C40 104.8(2) . . . . ?
C32 C31 C39 C40 -73.4(2) . . . . ?
C30 C31 C39 C44 -76.5(2) . . . . ?
C32 C31 C39 C44 105.3(2) . . . . ?
C44 C39 C40 C41 -0.8(3) . . . . ?
C31 C39 C40 C41 177.91(19) . . . . ?
C39 C40 C41 C42 0.1(3) . . . . ?
C40 C41 C42 C43 0.1(4) . . . . ?
C41 C42 C43 C44 0.3(3) . . . . ?
C42 C43 C44 C39 -1.0(3) . . . . ?
C40 C39 C44 C43 1.3(3) . . . . ?
C31 C39 C44 C43 -177.46(17) . . . . ?
C31 C30 C45 C46 99.5(2) . . . . ?
C29 C30 C45 C46 -82.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.025
_database_code_depnum_ccdc_archive 'CCDC 993171'
